Prostaglandins of the F series

Abstract

The present invention provides new compounds, 13,14-dihydro-15-keto-PGFs, and vassopressors containing them, which raise blood pressure without substantial ephemeral depression of blood pressure, trachea or enteron contraction effect inherent in usual PGFs.

What is claimed is: 
     
       1. A 13,14-dihydro-15-keto-PGF represented by the formula: in which a bond between C-2 and C-3 is a single or a double bond,   X is a group: ##STR37## R 1  is a hydrogen atom or a C 1-4  alkyl, phenyl, benzoyl, hydroxyalkyl, alkoxyalkyl, trialkylsilyl or tetrahydropyranyl group;   R 2  is a hydrogen atom or a lower alkyl group;   R 3  is hydroxyl;   R 3'  is hydroxyl;   R 4  and R 5  are the same or different, and signify a hydrogen atom, a halogen atom, or a lower alkyl group, and at least one of R 4  and R 5  is a halogen atom;   R 6  is a C 4-9  alkyl group which may be branched or contain a double bond, a C 1-9  alkyl group containing a C 1-2  alkoxy substituent or ##STR38## (wherein R 7  is a hydrogen or halogen atom or a halogenated methyl group); and a physiologically acceptable salt of said 13,14-dihydro-15-keto-PGF.   
     
     
       2. The 13,14-dihydro-15-keto-PGF according to claim 1, wherein R 1  is a C 1-4  alkyl group. 
     
     
       3. The 13,14-dihydro-15-keto-PGF according to claim 1 comprising a 13,14-dihydro-15-keto-16-substituted-PGF represented by the formula: ##STR39## wherein at least one of R 4  and R 5  is a halogen atom, or a physiologically acceptable salt thereof. 
     
     
       4. The 13,14-dihydro-15-keto-PGF according to claim 1, wherein each of R 4  and R 5  is a halogen atom, or a physiologically acceptable salt thereof. 
     
     
       5. The 13,14-dihydro-15-keto-PGF according to claim 1 comprising a 13,14-dihydro-15-keto-16,R,S-fluoro-PGF 1  α-methyl ester, or a physiologically acceptable salt thereof. 
     
     
       6. A 13,14-dihydro-15-keto-PGF of claim 1 being a 16 halo 13,14-dihydro-15-keto-20-ethyl-PGF 1 α, a C 1  -C 4  alkyl ester or a physiologically acceptable salt thereof. 
     
     
       7. A 13,14-dihydro-15-keto-PGF of claim 1 being a 16 halo 13,14-dihydro-15-keto-20-ethyl-PGF 1 α isopropyl ester.